Chatham, which is situated in the “elbow” of Cape Cod, is one of those rare small towns that feels like it was a cool small town 100 years ago. After all, you can’t avoid its history, and it involves lots of eye-catching sites. First, there’s the postcard-perfect Chatham Lighthouse, which is on the National Register of Historic Places. It was first lit to guide boats in 1897. The town's historic district has over 300 protected buildings. What’s more is the town has the highest concentration of classic Cape-Cod-style houses. (Think: timber frames, Victorian details) Not least among them is the ultra-luxe resort Chatham Bars Inn. Among its 24-plus buildings, some date back as far as 1914. Also onsite is eight acres of farm and a greenhouse, sources for the hotel’s posh restaurants’ produce and herbs.

While those kinds of gardens are above and beyond what most other restaurants in Chatham offer, one thing that pretty much every dining spot offers is straight-off-the-boat seafood. The town is an embarrassment of riches when it comes to lobster, haddock, and skate, to name a few. And about those restaurants—there’s a lot of them. It all starts at the airport, where you’ll find Hangar B, a compact eatery known for its hearty and creative breakfast fare. Other options throughout town range from the classy yet casual Bistro on Main to the Filling Station, a retro diner located downtown that dishes out classic breakfast food all day and burgers on soft pretzel buns, to the legendary Chatham Orpheum Theater, which features a café where you can anything from salads to burgers to sandwiches to sliders as well as beer, wine, and cocktails and indulge while you watch a movie.

Toss in plenty of outposts for birdwatchers (the Monomoy National Wildlife Refuge is part of the US Fish and Wildlife Services) to take in the show; the new Chatham Shark Center, in case you wanna learn more than you can get during "Shark Week" (Chatham is known for the return of great white sharks); and whale watching excursions and it all adds up to something pretty cool.

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